Becoming a Shemale Hooker: Chapter 4

callgirl3At first around my waist, gradually sliding down to my butt, Jack’s hand guided me through what seemed like countless doors and long corridors.  The click of my heels and the sway of my hips displayed a confidence I had not yet earned.  Like a virgin acting like a sexpot, down deep I knew I was a fraud, a fake, just a wanabee whore.  It wouldn’t take much to reignite the worries and fears I had felt initially when Jack’s creepy telephone voice was booking our date.

So when Jack ushered me, the nervous Nellie, into the inner sanctum of his executive suite and locked the door behind us, one of my heels snagged the edge of an Oriental carpet. I would have fallen had Jack not steadied me.  All the lady-like poise I had spent months, even years, cultivating quickly melted into embarrassment…and, yes, fear.

“Maybe I should call Marvin…” I stammered and reached into my purse for the cellphone. “… And tell him I’m here.”

“No need to do that, Joyce.”  He handed me an unsealed envelope.  “Put this in your purse instead.”  My fingers opened the envelope and flipped through the bills — four $100’s and one $50.  Just as Marvin — the escort service owner and so, yes, my pimp —  had said it would work!  My estrogen-patch-addled bimbo brain didn’t even have to remember to ask for the money!

What exactly was Jack buying for $450?  I wasn’t yet sure.  That was my appointment rate set by Marvin.  For that amount, the client could have up to one and one-half hours of my precious time.  If the client wanted additional time, it would be at the $300 hourly rate.  Overnight rates could be negotiated.

Everything had to be prepaid, either by credit card over the phone with Marvin or by handing cash directly to me.  If the latter, I would deposit Marvin’s one-third directly into his bank account the next morning at a bank branch most convenient to me.

I’ll tell you more about Marvin later, but at that particular moment I was in awe.  He had thought of everything — as slyly clever as any Wall Street hedge fund manager.  By paying upfront, the client could never be undercover police because that would be entrapment.  And by coordinating all the logistics of the appointment through Marvin’s office, I was reasonably safe: if I didn’t report in by phone in exactly one and one-half hours, Marvin would send one of his assistants looking for me.

Marvin had the address.  He had the client’s phone number, maybe even credit card number.  Marvin knew everything.  My fate was in his hands.  Suddenly I had a glimpse of the legendary power of a pimp:  Marvin had become my God-like protector.

Of course, Marvin at this very moment could not prevent Jack from raping me, killing me, then cutting me up into tiny pieces.  But if Jack was rational, he knew he would never get away with it….right?

Becoming a Shemale Hooker: Chapter 3

callgirl3Just as Mr. Jackson had instructed on the phone (in a hoarse and heavy-breathing voice), I pulled my car into the dark and mostly deserted office parking lot… and headed toward the illuminated place under the lamp-post.  There I was to park — in the spotlight under the lamp-post.  The phallic symbolism — I couldn’t help but smile — relieved at least some of my anxiety.  My next instructions were these:

Turn the car engine off.  Turn on the car’s inside lights.  Look in the rear-view mirror and start touching up my makeup, specifically my lipstick.  Wait for my cell to ring, which it now did just moments after I had deposited my lipliner back in my purse.

“Yes, Mr. Jackson…. Yes, Mr. Jackson…. Yes, of course, I want to make you happy.”   After his abrupt goodbye, I proceeded to do exactly as I had just been told:

Make believe I’m just a normal businesswoman arriving at a real job. Open the car door.  Stay seated, but swivel my legs so that my heels are on the pavement.  Make sure that my skirt is hiked up, so that an observer from the office building can see my crotch.

“Wear no panties!” he had earlier commanded.  Now I began to understand.  And I followed precisely the rest of his instructions:

Pretend I’m unaware of either the observer or the fact that my crotch is showing.  When I stand up, feint surprise that my skirt is hiked up so high; quickly tug it down to mid-thigh; look around, embarrassed, to make sure no one has seen me; then walk briskly, as if late for work, to the office entrance.

Buzzed through security, I then took the elevator to the second floor. There waiting for me as I exited the elevator was Mr. Jackson. I can’t describe exactly the man I had expected as my very first “John,” but he definitely wasn’t it!  And his voice no longer made me tremble:

“You’re beautiful,” he said — the binoculars still in hand that he had obviously used to spy on me arriving in the parking lot. “The agency’s photos don’t do you justice.”

“Thank you, Mr. Jackson.”

“Just call me Jack,” he said, holding the door open for me to step into Suite 210.

Becoming a Shemale Hooker: Chapter 2

callgirl3“Don’t wear any panties!” The scary, heavy-breathing voice over the telephone kept commanding.

How could this be? What was being asked of me? A male-to-female transsexual not wearing any panties?  That’s like a cappuccino without any foam…skinny jeans without fuck-me boots….  Why, I had spent all my life working up the courage just to wear panties!

It was as if he were asking me to cut off all my hair, which I had so religiously cultivated over the last couple of years…or commanding me to smear my impeccable makeup into the face of a clown….

But he would be paying me for my time, during which I would be expected to do exactly what he wanted of me, so I had to do what he asked, right? This wasn’t at all what I had bargained for when signing up with the well-established local escort service as their newest (and therefore presumably hungriest) “fully-functional” shemale hooker.

Marvin, the founder and owner of the escort service, seemed to take a special interest in “the new girl” and tried to reassure me:

“Mr. Jackson is a regular client. He always wants to check out the new girls. If you do what he wants and he likes you, it’ll be a regular gig. And that can be very lucrative.  He tips extremely well.”

“But he doesn’t want me to wear any panties!” I protested.

“Believe me, he’s totally harmless…. You’ll see. He’s kind of pitiful, actually.” Marvin then held my hand, as it were, by gaming out the scenario in which I was to be the leading lady:

“Mr. Jackson is an older gentleman who owns his own business. As you drive into the parking lot, he’ll be watching from his office on the second floor. I think he even has binoculars. The idea is for you to be very femininely, professionally dressed as if arriving for work, yet underneath having your male genitals hanging out. He apparently gets his kicks from knowing what no one else knows watching you….

“If you look like a drag queen or you can’t pass, he’ll send you away. He might give you a tip, but he won’t pay for the full one and half-hours.” Marvin paused. “Don’t worry, baby, you’ll do fine.”

Still, I just couldn’t imagine getting all dolled up and not having the most basic feminine foundation securely underneath. How could I look and feel feminine if my nuts are swinging while I sashay across the parking lot? Admittedly, the flesh-colored pantyhose that Mr. Jackson had instructed me to wear would hold things somewhat in place. But without tightly tucked panties, there might well be a decidedly unfeminine bulge against the tight skirt I had also been instructed to wear.

It would take 30 minutes or so of driving in the evening rush hour to reach Mr. Jackson’s office in a suburban business park. The traffic was made worse by a heavy rain. I was dressed exactly as instructed, sans culotte. But tucked, like a security blanket, in my purse by my side on the front seat was a brand-new pink pair of Victoria’s Secret bikini briefs, a nice and snug size six.

When I got lost — just like the good bimbo I was striving to be! — I seriously considered turning the car around and telling Marvin I just didn’t feel right about things. Perhaps he would let me try someone besides Mr. Jackson as my very first John? But I knew Marvin well enough to know that he was all about the money, that Mr. Jackson was one of his most valued regular clients, and that my cowardice would no doubt be a career-ender.

I often wonder how my life now would be different if I had in fact turned around that rainy spring evening — and not kept going down the (rush-hour-clogged) road of becoming a shemale hooker?

Becoming a Shemale Hooker: Chapter 1

Today’s flaneur doesn’t even have to leave home but can just “stroll” around the Internet. For an uninhibited woman like me — whose self-esteem can too often be measured in the height of my fuck-me high heels — staying glued to a computer screen is no fun at all, however.

I want to be seen as much as I want to see others. Without their eyes validating my sex appeal — my very sense of self! — I sometimes wonder if I’d even exist. I might as well be dead. Validation comes not simply with the male gaze, but most especially with the cocks that I make hard.

So it is that when you’ve had sex with as many men as I have, it’s hard to go anywhere without spotting a familiar face. Of course, across the ocean, in faraway cities, it’s highly unlikely they are the actual guys I have known…and been oh so intimate with. But occasionally they can certainly look alike — sometimes scarily so — so much so as to cause me to do a double-take, catch my breath, and feel, against my conscious will, the memories flow.  Not unlike the way an old tune suddenly coming on the car radio can transport you backwards, time-traveling — making yesterday even more real than today.

Take the apparition I see now at the coffee shop while I’m sipping my latte and my eyes glancing up from my laptop:

The ugly, old guy sitting at the cafe table not talking to the unhappy woman sitting across from him (she must be his wife).  He looks exactly like my very first trick!  How extraordinary.

How can I ever forget him?

I can still feel the fear as I drove to the rendezvous that spring evening.  I was wearing precisely what he had instructed me to wear when he booked the “date” — long, elegant jacket; with matching short, tight skirt; strappy high heels (of course); flesh-colored pantyhose but no panties. “Absolutely do not wear any panties!  Do you understand?” His insistent voice on the telephone, hoarse and heavy, really did frighten me.

I must continue this journal entry later as I, in the here and now, have another date, yet another, totally different man to please and so please me.  But I will say this for the moment: I’m no longer frightened…..

“A Binder Full of Shemales”

sec4If I can’t make it as a porn star, I’ll settle for being a sexy secretary.

My years working as a high-end escort have well prepared me for this newest role. Classy yet slutty, Bimbo-like but actually probably smarter than my boss (clients), I’ve got the part down pat.

My attitude might seem appalling to feminists. But I’m just so happy to get the job, particularly given the employer’s unconscionable lack of “a binder full of shemales.” (It’s not as if we expect maternity leave coverage or anything.)

Shemale Schooling: Makeup and Cum Can Mix!

makeupDear Mistress Joy, Your Ladyship:

When men cum on my face, it makes a horrible mess of my make-up. So in order to still look pretty while sucking still more cock, I have to interrupt everything, ruining the romance, in order to run into the bathroom and take valuable time rebuilding my foundation! By the time I return, the cock is often no longer hard. What can I do?

Joy’s Gems (of Wisdom):
If cum on your face is creating a mud-like mess, obviously you’re using a lot of foundation! Which, of course, is necessary if you didn’t start ingesting girlie hormones until after puberty and your electrolysis or laser treatments are still incomplete. (I wonder if the guys giving you facials appreciate how expensive and pain-in-the-ass these treatments are, to eliminate one’s beard to make one’s face more fuckable!)

Anyway, the key variable is not how much foundation you use — but how you apply it.  No matter how much residue roughness you need to hide, you just don’t want to slap and cake liquid foundation all over your face. Remember your makeup basics: Less is more!

Start with a very light base. Don’t smear it all over your face. Rather, apply from the tips of your fingers tapping gently until your face is covered. Then when dry, use a big fluffy brush to dust powder on that first layer of foundation.

Then keep layering and layering and layering: thin coats of foundation followed by dustings of powder. It takes time and patience; but the result is so polished, your feminine face will look like a runaway model’s.

And it will retain that polished look even with gobs of cum all over your face. The trick is not to smear the cum — but to let it dry and cake over your makeup. To prevent huge globs of cum from trickling down your face before they dry, simply dab them with a tissue to remove the excess. Dab!  Don’t rub, wipe, and smear!

Then, to go out in public with subtle spots of dried cum dotting my face — I find incredibly sexy! And all the other girls become so, so jealous. They all want to be shemales!

My Mystery Lover at 30,000 Feet

mile_high_club_stewardess_1__36829_zoomHow can it be? How can it be that the man who gave me the most intense orgasm I’ve ever experienced remains unknown to me? Ah, to be ravished by a total stranger, that’s exciting enough…but more…there’s so much more to the story. Or perhaps I should say “less.”

For he never even touched me! And only afterwards did I see him. I just had to see his face. Who was this “masked” man?

So I tapped him on the shoulder, as we were all standing up in the aisle, after the eight-hour transatlantic flight, to file out of the airplane. He turned his head. I smiled, and mouthed, “Thank you. Thank you very much.” He blushed. Only then, it seemed, did he realize the pleasure he had given me — my phantom pilot.

To fly, to soar, to spread my wings (and legs) — with my phantom pilot at the controls. That’s what had happened high above the dark ocean — maybe Iceland — as the sun would soon rise over the coast of France.

But, actually, my phantom pilot was only nominally in control. I had planned it all, down to the last detail. My pleasure had been premeditated. I knew exactly what I wanted: to make a long-anticipated fantasy come true.

It started with how I decided to dress that day, well before the taxi came to take me to JFK. I usually don’t wear flouncey skirts, but anything too tight might have revealed the bulge in my crotch. The bulge wouldn’t have been from my residual cock (we so-called shemales are well practiced in disguising that!). Rather, it was the sextoy called “The Scorpion,” strapped to the furtherest reaches of my upper thighs. (For a complete description of The Scorpion’s magicial properties, please see earlier blog post “My New Best Friend.”)

I was in control.  I knew exactly what I wanted.  He was totally unaware — just a tool, an extension (literally) of my sextoy.  Man as sextoy: I like that!



Another Year in Fantasyland: Getting Paid for What You Love to Do!

RISTMA~1“Fantastic!” People often reply when I ask how I look. Or I will say “Fantastic!” when asked how I feel.

It’s a most appropriate adjective for girls like me, whose whole life could be described as a fantasy. And once embarked upon that fantasy – the boy who actually lives the impossible dream of becoming a girl! — I find it hard to reject any fantasy, no matter how flighty, that ever darts into my silly, unpredictable brain.

Take prostitution, for instance. Just about every real woman I know readily acknowledges that she sometimes fantasizes about getting paid for sex. But she never actually acts out the fantasy. “Of course, not!” she exclaims. “I’m not crazy.” Or: “I’m not that sinful.”

But for me, it’s no big deal after the crazy — arguably sinful — journey I’ve already embarked on. That train has already left the station. Or, for a more appropriate metaphor – given everyone’s recurring fantasy of joining the “mile-high club” – the plane has already taken off.

“Selling my body,” as people put it, I’ve never found degrading. To the contrary, it’s validating. Maybe that’s because I’m never really selling my body. I’m just cashing in on a fantasy, not mine but theirs. To the men who pay me, I’m their ultimate fantasy chick.

Not unlike being a Playboy centerfold whose image sparks countless masturbatory fantasies – and fulfillments! The only difference is that the cum splashes and smears glossy magazine paper, while the cum aimed at me is captured in a condom.

New Year Resolutions

sexy_happy_new_year_2008_shirtToo bad it’s not Leap Year. Then the number would be 366 — not 365. The number of sex partners I resolve to have in the upcuming year!

Or should my resolution be simply to return triumphantly to the annual Oral Sex World Championship? And this time bring back a Gold! Not a mere “second runner-up” title.

Only teasing….

For, alas, we’ve all seen the spectacle of too many Olympic-level athletes compete well past their prime. As for the number of my fuck partners, I’ve reached the age when quality is definitely more important than sheer quantity. I wouldn’t mind having sex at least once a day for the next 365 days, of course; but I’d like to be able to remember the name (the real name, too!) of the individual person behind each unique cock I suck.

So maybe my New Year’s Resolution should be to go ahead and commit to one special cock — that is, get married! Me as the blushing bride!

How sexy! Even sexier, maybe, would be for me to write the Greatest Memoir of all time. And each one of these blog entries is like one (sometimes tiny) suckable cock on the way to my ultimate goal….

My New Best Friend

scorpiontattooToday, boys and girls, the subject is sextoys.

My newest best friend is a Scorpion! That’s the name for the most incredibly pleasureable sextoy I’ve ever enjoyed, and only now  just discovered. It straps between my legs at the furtherest reaches of my upper thighs. Its curved tail reaches around to tickle my bottom. Its head and pinchers clasp my clit (an extra big “clit,” as you well know, given my pre-opt condition).

Then — and here’s the very best part — from the scorpion itself runs a long wire, perhaps a meter or a yard in total length. At the other end of the wire is the master control switch, which with the mere flick of a finger or thumb commands the scropion tail and pinchers to vibrate madly. Depending upon the mood of whoever’s fingers control the master switch, the vibration is set at a high, medium, or low speed.

“Designed by a woman for women!” The advertisement must be true.

My fantasy — and one that I seriously intend to act out very shortly — is to have strapped the scorpion on underneath my panties and skinny jeans when I next board an airplane. Once seated and airborne, Ill hand my traveling companion the scorpion control knob.

This will arguably give him almost as much pleasure as I — to be in control and to experience vicariously at least the kind of sextoy-induced pleasure that girls only are privilege to know. (Doing it in a public place helps, too!)

For my newest profound thought, or philosophical thesis, is that men are limited in their self-gratification to visual images, evidenced especially in porn. This makes sense, since the objects (yes, accept the fact, we girls are objects!) of men’s desire are physically separate — and thus must be seen in order to be then taken, possessed, devoured…or whatever.

For girls, on the other hand….

The precise moment when I knew what womanhood probably meant was when I closed my eyes and allowed myself to feel the need to be touched — and, most especially, filled!  That’s what happiness is!

I didn’t need to see any pictures, pornographic or otherwise, visualizing myself as a sex object. A sextoy, instead, awakened the woman within.

To be sexually excited…oh-so excited…I just needed a vibrating dildo…blessing me so: Just to close my eyes and feel the feeling…feel the filling!

And so it is now: Oh, how I love you, my scorpion!